Winthrop Vacations from $695

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The Latest Winthrop vacation packages

Price found within the past 48 hours. Click for updated prices.
Isle Casino Hotel - Waterloo - A Caesars Rewards Destination

Isle Casino Hotel - Waterloo - A Caesars Rewards Destination

3 out of 5
Price was $816, price is now $695 per person
$695
per person
Jun 12 - Jun 15
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Waterloo (ALO)
8.2/10 Very Good! (1,003 reviews)
staff was very friendly. we stayed for 1 night.. comfortable beds, rooms at spacious. there was a dirty pair of pants and underwear left in the dresser.

Reviewed on Apr 13, 2026

Cobblestone Inn & Suites – Manchester

Cobblestone Inn & Suites – Manchester

3.5 out of 5
Price was $810, price is now $696 per person
$696
per person
Jun 11 - Jun 14
found 12 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Waterloo (ALO)
9/10 Wonderful! (347 reviews)
The staff was extremely helpful and the breakfast was amazing!

Reviewed on Apr 3, 2026

The Black Hawk Hotel

The Black Hawk Hotel

3.5 out of 5
Price was $793, price is now $720 per person
$720
per person
Jun 12 - Jun 15
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Waterloo (ALO)
9.2/10 Wonderful! (822 reviews)
Wonderful hotel, very nice bar tender and wonderful drinks. Especially enjoyed the full old world decor. Only downside was the air system in the room I was in was a little loud as it had a large duct. But I will take heat and cool over sound.

Reviewed on Apr 14, 2026

Comfort Suites Cedar Falls Industrial Park

Comfort Suites Cedar Falls Industrial Park

2.5 out of 5
Price was $831, price is now $757 per person
$757
per person
Jun 12 - Jun 15
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Waterloo (ALO)
8.6/10 Excellent! (957 reviews)
Breakfast was the same menu two days in a row, but still good

Reviewed on Apr 16, 2026

The Weis Mansion

The Weis Mansion

3 out of 5
Price was $812, price is now $744 per person
$744
per person
Jun 12 - Jun 15
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Waterloo (ALO)
10/10 Exceptional! (46 reviews)
A beautiful home and a spacious comfortable room. The breakfast was excellent. Hosts are friendly and engaging. Would definitely stay here again.

Reviewed on Mar 26, 2026

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Winthrop Hotel Deals

Cornerstone Inn & Suites

Cornerstone Inn & Suites

2.5 out of 5
421 Rock Island Road Oelwein IA
Fully refundableReserve now, pay when you stay
$105 nightly
The price is $117 total per night from Apr 19 to Apr 20
$117 total
Apr 19 - Apr 20
Total with taxes and fees
9.2/10 Wonderful! (494 reviews)
Clean, comfortable room and friendly staff

Reviewed on Apr 13, 2026

Cornerstone Inn & Suites
Cobblestone Inn & Suites – Manchester

Cobblestone Inn & Suites – Manchester

3.5 out of 5
1210 Commercial Court Manchester IA
Fully refundableReserve now, pay when you stay
$102 nightly
The price is $115 total per night from Apr 24 to Apr 25
$115 total
Apr 24 - Apr 25
Total with taxes and fees
9/10 Wonderful! (349 reviews)
Please teach them how to make coffee. I love my coffee but did not like the coffee there! it was full of Grounds! I am not sure what was going on! My husband also used little pot in our room and said it also had grounds in even though it had packaged coffee to use that was disposable. Otherwise stay ...

Reviewed on Apr 16, 2026

Cobblestone Inn & Suites – Manchester
Urbana Inn & Suites

Urbana Inn & Suites

2.5 out of 5
5369 Hutton Drive Urbana IA
$79 nightly
The price is $83 total per night from Apr 19 to Apr 20
$83 total
Apr 19 - Apr 20
Total with taxes and fees
8.4/10 Very Good! (326 reviews)
Friendly and professional staff, older property but very clean and comfortable. I appreciate the pet friendliness and reasonable add on charge for that service. The hotel stuck me as a family owned small business, with clear pride of ownership. Would stay again no question.

Reviewed on Apr 3, 2026

Urbana Inn & Suites
See all 59 properties in Winthrop
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Find the Best Winthrop Vacation Packages

Winthrop Essential Information

Language
English
Currency
U.S dollars
Population
850
Max Temp Winter
25ºF
Max Temp Summer
80ºF

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Frequently asked questions

How much does a Winthrop vacation package cost?
You'll find cheap prices from $695 on Expedia for your Winthrop getaway. However, a range of factors like the hotel choice, length of stay and season will influence how much your vacation to Winthrop costs.
What are the cheapest months to go to Winthrop?
December, January and February are the best times to look for cheap Winthrop vacation packages. Traveling in quieter months means you can typically find lower prices on flights and accommodations.
How many days is enough for Winthrop?
Generally, a handful of days is enough to check out the major attractions during your Winthrop vacation. But if you'd like to have some time to rest or take day tours, consider extending your trip.
How to find the best Winthrop package deals?
Use Expedia's handy filters to help you find some fabulous Winthrop package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your break for midweek, or search for Winthrop package deals in the low season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to book your vacation package as early as possible.
Is it cheaper to book a Winthrop vacation as a package?
You can enjoy significant savings on your Winthrop break by booking a personalized vacation package. Click on the "Package" heading, then select your destination and travel dates to see some great hotel and flight prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Winthrop?
If you're considering a spur-of-the-moment Winthrop adventure, check out our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can land amazing deals on your hotels and flights by booking ahead.
Does Expedia offer Book Now, Pay Later Winthrop vacation packages?
Set off on your perfect trip to Winthrop with help from Expedia's Book Now, Pay Later vacations. There's no need to save up or hold off until payday — we've partnered with online lender Affirm to give you financial flexibility. Our vacation packages with payment plans allow you to split the cost across 3, 6 or 12 months. With no hidden or late payment fees, it's easy to budget for your trip and snap up travel deals before they sell out.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.